Phaselic acid, (-)-

Details

• Internal ID: 54cfdf9b-f83e-4aa4-95b2-a2c386b79038
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: (2R)-2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxybutanedioic acid
• SMILES (Canonical): C1=CC(=C(C=C1C=CC(=O)OC(CC(=O)O)C(=O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C/C(=O)O[C@H](CC(=O)O)C(=O)O)O)O
• InChI: InChI=1S/C13H12O8/c14-8-3-1-7(5-9(8)15)2-4-12(18)21-10(13(19)20)6-11(16)17/h1-5,10,14-15H,6H2,(H,16,17)(H,19,20)/b4-2+/t10-/m1/s1
• InChI Key: PMKQSEYPLQIEAY-XCRNYIDWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₁₂O₈
• Molecular Weight: 296.23 g/mol
• Exact Mass: 296.05321734 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 0.58
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

• W3PJ394QLY
• UNII-W3PJ394QLY
• 423170-79-0
• (2R)-2-(((2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)butanedioic acid
• Butanedioic acid, (((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (2R)-
• Butanedioic acid, 2-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-, (2R)-
• (2R')-Phaselic acid
• SCHEMBL21191515
• (R)-2-(3,4-Dihydroxycinnamoyloxy)succinic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9431	94.31%
Caco-2	-	0.8630	86.30%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7286	72.86%
OATP2B1 inhibitior	-	0.7154	71.54%
OATP1B1 inhibitior	+	0.9447	94.47%
OATP1B3 inhibitior	+	0.9580	95.80%
MATE1 inhibitior	+	0.5200	52.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6518	65.18%
P-glycoprotein inhibitior	-	0.9595	95.95%
P-glycoprotein substrate	-	0.9547	95.47%
CYP3A4 substrate	-	0.5935	59.35%
CYP2C9 substrate	-	0.5979	59.79%
CYP2D6 substrate	-	0.8612	86.12%
CYP3A4 inhibition	-	0.9113	91.13%
CYP2C9 inhibition	-	0.9697	96.97%
CYP2C19 inhibition	-	0.9669	96.69%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	-	0.9086	90.86%
CYP2C8 inhibition	+	0.4603	46.03%
CYP inhibitory promiscuity	-	0.9779	97.79%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8575	85.75%
Carcinogenicity (trinary)	Non-required	0.6600	66.00%
Eye corrosion	-	0.9477	94.77%
Eye irritation	+	0.5540	55.40%
Skin irritation	+	0.5109	51.09%
Skin corrosion	-	0.8843	88.43%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7674	76.74%
Micronuclear	+	0.8018	80.18%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	+	0.7296	72.96%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8524	85.24%
Acute Oral Toxicity (c)	III	0.7214	72.14%
Estrogen receptor binding	+	0.6047	60.47%
Androgen receptor binding	+	0.8555	85.55%
Thyroid receptor binding	-	0.7392	73.92%
Glucocorticoid receptor binding	-	0.4704	47.04%
Aromatase binding	-	0.5829	58.29%
PPAR gamma	-	0.5902	59.02%
Honey bee toxicity	-	0.8586	85.86%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6455	64.55%
Fish aquatic toxicity	+	0.9618	96.18%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.30%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.97%	96.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.19%	99.15%
CHEMBL3194	P02766	Transthyretin	92.67%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.53%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.62%	99.17%
CHEMBL2581	P07339	Cathepsin D	91.20%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.04%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.49%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	85.80%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.09%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.67%	89.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.24%	94.62%

Plants that contains it

• Abies veitchii
• Ainsliaea macrocephala
• Boronia ternata
• Buxus microphylla
• Buxus sempervirens
• Casearia membranacea
• Cephalaria ambrosioides
• Chamaecytisus ratisbonensis
• Cinnamomum kotoense
• Colchicum robustum
• Conospermum teretifolium
• Dicoma anomala
• Epidendrum rigidum
• Galeopsis tetrahit
• Liochlaena subulata
• Luculia pinceana
• Marrubium velutinum
• Marrubium vulgare
• Nepeta cataria
• Panzerina lanata
• Parietaria officinalis
• Pinus mugo
• Pityrogramma ebenea
• Pyrus pyrifolia
• Strychnos camptoneura
• Trifolium pratense
• Trifolium subterraneum
• Vellozia nivea
• Zanthoxylum ailanthoides

Cross-Links

• PubChem: 92299542
• NPASS: NPC157721
• LOTUS: LTS0169052
• wikiData: Q105211547